Sodium Azide → HCID 58504435, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of crude [(2S,5R)-4-(2-amino-6-chloro-4-pyrimidinyl)-5-methyl-2-morpholinyl]methyl methanesulfonate (1.53 g, about 85% pure, 3.88 mmol) and sodium azide (0.382 g, 5.88 mmol) in DMF (75 mL) was stirred at 80° C. under nitrogen for 20.5 hours. Another portion of sodium azide (0.094 g, 1.45 mmol) was then added and stirring continued at 80° C. for an additional 6.5 hours. The mixture was then cooled, diluted with EtOAc (200 mL), washed with water (2×150 mL) and brine (1×150 mL), dried (Na2SO4), filtered, and concentrated in vacuo. The residue was purified by flash chromatography (60 g SiO2, 1:1 hexanes/CH2Cl2 to 45:45:10 hexanes/CH2Cl2/CH3CN gradient) to give the title compound (890 mg) as a thick colorless oil. LC-MS (ES) m/z=284, 286 [M+H]+.

Provenance & Evidence